4'-Bromoacetophenone

Chemical properties

white to light yellow crystals. soluble in alcohol, ether, glacial acetic acid, benzene, carbon disulfide and petroleum ether, insoluble in water. Easy to volatilize with water vapor.

The Uses of 4'-Bromoacetophenone

4'-Bromoacetophenone is an important organic synthesis intermediate, widely used in synthetic medicine, pesticides, dyes, flavors and fragrances, perfumes, Intermediates of Liquid Crystals etc.

The Uses of 4'-Bromoacetophenone

Labeled 4?-Bromoacetophenone possess activity against positive phototaxis of Chlamydomonas cells. A fundamental starting material for organic synthesis.

Preparation

4'-Bromoacetophenone is synthesized by the reaction of bromobenzene and acetic anhydride in the presence of aluminum trichloride.
Add bromobenzene and dry carbon disulfide into the reactor, put in powdered anhydrous aluminum trichloride, heat until it starts to reflux, stop heating, add acetic anhydride dropwise, and then reflux for 1 hour after adding, steam out carbon disulfide, and put it while it is still hot. The reactant was poured into the hydrochloric acid ice-water mixture, filtered to dryness, and distilled under reduced pressure to obtain p-bromoacetophenone.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 5400, 1986 DOI: 10.1021/jo00376a064
Tetrahedron Letters, 26, p. 4657, 1985 DOI: 10.1016/S0040-4039(00)98778-1

Purification Methods

Crystallise it from EtOH, MeOH or from pet ether (b 80-100o). [Tanner J Org Chem 52 2142 1987, Beilstein 7 IV 647.]